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WO2004100682A1 - Nouvelle composition de sel de metal complexe d'acide garcinique, methode de preparation et d'utilisation de la composition - Google Patents

Nouvelle composition de sel de metal complexe d'acide garcinique, methode de preparation et d'utilisation de la composition Download PDF

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Publication number
WO2004100682A1
WO2004100682A1 PCT/IN2003/000192 IN0300192W WO2004100682A1 WO 2004100682 A1 WO2004100682 A1 WO 2004100682A1 IN 0300192 W IN0300192 W IN 0300192W WO 2004100682 A1 WO2004100682 A1 WO 2004100682A1
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WO
WIPO (PCT)
Prior art keywords
acid
composition
hca
calcium
metal salt
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2003/000192
Other languages
English (en)
Inventor
Samuel Philip
Saravanan Somasundaram
Thangaraj Meyyappan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Indfrag Ltd
Original Assignee
Indfrag Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Indfrag Ltd filed Critical Indfrag Ltd
Priority to PCT/IN2003/000192 priority Critical patent/WO2004100682A1/fr
Priority to AU2003241151A priority patent/AU2003241151A1/en
Priority to US10/822,867 priority patent/US7214823B2/en
Publication of WO2004100682A1 publication Critical patent/WO2004100682A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/16—Inorganic salts, minerals or trace elements
    • A23L33/165—Complexes or chelates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/28—Compounds containing heavy metals
    • A61K31/315—Zinc compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/38—Clusiaceae, Hypericaceae or Guttiferae (Hypericum or Mangosteen family), e.g. common St. Johnswort
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/82—Theaceae (Tea family), e.g. camellia

Definitions

  • the invention relates to new composition comprising complex metal salt of garcinia acid, a process for preparing the same and use in dietary supplements, nutraceuticals, food products and beverages for promoting weight loss.
  • the invention also relates to the preparation process of penta, tetra, tri, double metal salt of garnicia acid.
  • Garcinia acid comprising (-)hydroxycitric acid (HCA), its lactone and Citric acid occurs in the fruit rind of Garcinia species (Garcinia cambogia, G. indica, G. atrovirdis).
  • Garcinia cambogia G. indica, G. atrovirdis
  • the fruit is known as "Kokum” and is used as a souring agent for pork and fish dishes.
  • the extract of the fruit rind is used to improve digestion and in cooking, for the preparation of curries.
  • the fruit rind of Garcinia is a rich source of (-)hydroxycitric acid, its lactone (10 to 30 %) and citric acid.
  • (-)Hydroxycitric acid prevents the conversion of excess carbohydrates to fatty acids by inhibiting the actions of cytoplasmic (cytosolic) ATP: citrate-lyase enzyme (D. Cloutre and M.E. Robenbaum, The Diet and Health Benefits of HCA, 1994) which plays key role in the conversion of carbohydrates to fatty acids and cholesterol (Sullivan et al., Lipids, vol. 9, pp. 121 and 129 (1973).
  • (-)hydroxycitric acid is not stable and is converted to the more stable lactone form during processing.
  • the free acid is stabilized by converting it into a salt form viz., sodium, potassium, magnesium, calcium and zinc by reacting with the respective base.
  • Free (-)hydroxycitric acid is released when the salt is dissolved in an acid.
  • the recommended daily intake (RDI) of calcium, potassium, magnesium and zinc element islOOO mg, 3500 mg, 400 mg and 15 mg respectively.
  • Most of the weight loss formulations employ these salts in the form of their inorganic metal salts.
  • these mineral supplements it is preferred to incorporate these mineral supplements as a single complex salt of HCA viz (Ca,K,Mg,Zn)HCA.
  • HCA complex metal salt
  • complex metal salt e.g. triple and tetra salt of HCA, which can act synergistically in weight management.
  • the complex metal salt should be highly soluble in water, non-hygroscopic and stable in solution.
  • Zinc salt of (-)hydroxycitric acid there is no prior art, which can supply HCA in the form of complex metal salt e.g. triple and tetra salt of HCA, which can act synergistically in weight management.
  • the complex metal salt should be highly soluble in water, non-hygroscopic and stable in solution.
  • Zinc salt of (-)hydroxycitric acid there is no prior art, which can supply HCA in the form of complex metal salt e.g. triple and tetra salt of HCA, which can act synergistically in weight management.
  • the complex metal salt should be highly soluble in water, non-hygroscopic and stable in solution.
  • Zinc salt of (-)hydroxycitric acid there is no prior
  • the goal of the present invention is to provide a composition of complex metal salt of (-)Hydroxycitric acid either alone or in combination with lactone of HCA and Citiric acid comprising all possible mineral supplements such as sodium, potassium, calcium, magnesium and zinc on a Recommended Daily Intake (RDI) basis.
  • An unique aspect of the present invention is the Zinc salt of (-)hydroxycitric acid which is not found in the prior art.
  • Another kind of complex metal salt can be manufactured by keeping the pH of the final product below 4, in which case the product will contain a combinatin of HCA and lactone of HCA.
  • the uniqueness of this low pH product is that it can be formulated in carbonated beverages in which the pH is maintained below 4 for stability. Also this novel product is suitable for use in food products without affecting their flavour and taste.
  • this low pH composition can be blended in any proportion with green tea extract having polyphenols content between 30 to 98 %.
  • Polyphenols are unstable in basic solutions and the insoluble calcium salt of (-)Hydroxy-citric acid can not be used . Since polyphenols are stable in acidic pH, the low pH soluble complex metal salt of (-)hydroxycitric acid can be effectively formulated with polyphenols to promote weight loss and delay ageing process.
  • hydroxycitric acid is a tricarboxyllic acid, which provides a very good means to incorporate preferred mineral supplement in the form of salt of hydroxycitric acid.
  • the present invention strives to provide a convenient method for the preparation of complex metal salt of HCA and subsequent formulation in dietary supplements, nutraceuticals, food products, beverages and in combination with other natural extracts preferred in weight management.
  • the complex metal salt of (-)hydroxycitric acid and its lactone is prepared from water extract of Garcinia and a mixture of bases selected from oxides, bicarbonates, carbonates, hydroxides of sodium, potassium, calcium, magnesium and zinc.
  • This complex metal salt of HCA can be prepared conveniently as a highly soluble or partially soluble or insoluble salt in water.
  • the product is essentially non-hygroscopic and stable in solutions and has the following composition: Table 1:
  • the complex metal salt of (-)hydroxycitric acid and its lactone can be manufactured by an economically viable process.
  • the Garcinia rind is extracted with demineralised water at room temperature.
  • the boiling or hot extraction used in prior arts gives an extract liquid that is enriched with unwanted water soluble components.
  • the invention minimizes the unwanted soluble matter by extracting the rind at room temperature.
  • the extract liquid is treated with calcium base to neutral pH to get insoluble calcium hydroxycitrate.
  • the HCA content of this insoluble material is approximately 70 %. If the neutralization is done at pH more than 7, the HCA content in the resulting insoluble salt will be 50 - 60 % only.
  • the insoluble calcium salt of HCA is mixed with water and 10 % sulphurous acid is added to remove the calcium as insoluble calcium sulphite.
  • the pH is maintained at 3.0 to 3.5 during this operation.
  • Prior art employ phosphoric acid in which case calcium Cannot be removed as insoluble salt because both HCA and phosphoric acids are weak acids and exchange reaction will not take place.
  • the filtrate liquid, light brown in colour is treated with preferred mixture of bases to neutral pH, charcoalised, filtered and spray dried to get white to off-white complex metal salt of HCA with or without the lactone of HCA.
  • This product is highly soluble in water (more than 20 %), non-hygroscopic and stable in solution.
  • Citric acid 2.40 %
  • Citric acid 1.90 %
  • a mixture of bases comprising 2.8 kg of magnesium hydroxide, 0.4 kg of zinc carbonate and 2.35 kg of calcium hydroxide was made into a slurry with 35 liters of demineralised water and added to 80 liters of Liquid HCA, in small portions at a time, over a period of 4 hours.
  • the partially neutralized solution was spray dried by maintaining the inlet temperature at 180°C to give 10.8 kg of Off-white crystalline powder with the following composition:
  • Citric acid 2.20 %
  • Citric acid 2.90 %

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Mycology (AREA)
  • Engineering & Computer Science (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Biotechnology (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne une nouvelle composition de sel de métal complexe d'acide garcinique, qui comprend: de l'acide hydroxycitrique (HCA), du lactone de HCA et d'acide citrique, et un mélange d'ions métalliques penta (5) ou tétra (4) ou triple (3) ou double (2) utilisables dans des compléments alimentaires diététiques, des nutraceutiques, des produits alimentaires et des boissons favorisant la perte de poids. Dans ladite composition la concentration du HCA est comprise entre 40 et 75 %, la concentration du lactone du HCA est comprise entre 0,1 et 30 %, la concentration de l'acide citrique est comprise entre 1 et 5 %, le reste étant constitué des ions métalliques choisis parmi sodium, potassium, calcium, magnésium et/ou zinc. L'invention concerne également l'utilisation de ladite composition dans des compléments alimentaires diététiques, des nutraceutiques, des produits alimentaires et des boissons destinés à favoriser la perte de poids. L'invention concerne en outre une méthode de préparation de la composition.
PCT/IN2003/000192 2003-05-19 2003-05-19 Nouvelle composition de sel de metal complexe d'acide garcinique, methode de preparation et d'utilisation de la composition Ceased WO2004100682A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/IN2003/000192 WO2004100682A1 (fr) 2003-05-19 2003-05-19 Nouvelle composition de sel de metal complexe d'acide garcinique, methode de preparation et d'utilisation de la composition
AU2003241151A AU2003241151A1 (en) 2003-05-19 2003-05-19 A novel composition of complex metal salt of garcinia acid, a process for preparing the same and use thereof
US10/822,867 US7214823B2 (en) 2003-05-19 2004-04-13 Hydroxycitric acid complex metal salts, composition, and methods

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000192 WO2004100682A1 (fr) 2003-05-19 2003-05-19 Nouvelle composition de sel de metal complexe d'acide garcinique, methode de preparation et d'utilisation de la composition

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US (1) US7214823B2 (fr)
AU (1) AU2003241151A1 (fr)
WO (1) WO2004100682A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007010838A1 (fr) * 2005-07-15 2007-01-25 Nippon Shinyaku Co., Ltd. Procédé servant à produire un sel de métal alcalinoterreux de l'acide (-)-hydroxycitrique
WO2018049216A1 (fr) 2016-09-08 2018-03-15 Glykon Technologies Group, Llc Composés d'acide hydroxycitrique bimétalliques monomères et leurs procédés de fabrication et utilisation
US11292759B2 (en) * 2018-03-07 2022-04-05 Nutrition Research Group, Limited Hydroxycitric acid metal heterocyclic compounds with covalent characteristics

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL1942874T3 (pl) 2005-11-04 2014-03-31 Omega Pharma Innovation & Dev Nv Kompozycja ziołowa do kontrolowania masy ciała
US10179157B2 (en) * 2015-02-16 2019-01-15 Phytotech Extracts Private Limited Slim and aqua concentrate having standardized and triple salt stabilized (−)-Hydroxycitric acid from Garcinia cambogia extract for making concentrate and slimming water and their derived product for weight management

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US5536516A (en) * 1994-08-24 1996-07-16 Renaissance Herbs, Inc. Hydroxycitric acid concentrate and food products prepared therefrom
EP0866137A1 (fr) * 1997-03-17 1998-09-23 Lupin Laboratories Limited Procédé de préparation de (-)-érythrohydroxycitrate de calcium
US6147228A (en) * 1998-08-03 2000-11-14 Department Of Science And Technology Government Of India Convenient method for the large scale isolation of garcinia acid
US6221901B1 (en) * 1996-10-22 2001-04-24 Ravi Shrivastava Magnesium (-)hydroxycitrate, method of preparation, applications, and compositions in particular pharmaceutical containing same
US6395296B1 (en) * 1997-08-08 2002-05-28 Karanam Balasubramanyam Soluble double metal salt of group IA and IIA of hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties
US6482858B1 (en) * 2001-06-20 2002-11-19 Dallas L Clouatre (−)-hydroxycitric acid for wound healing and immunomodulation

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US3764692A (en) 1970-09-30 1973-10-09 Hoffmann La Roche Method of treating obesity
US5612039A (en) 1994-03-14 1997-03-18 Nini E. Policappelli Dietary supplement
AU5736096A (en) 1995-05-15 1996-11-29 Sabinsa Corporation A new process for the production of potassium hydroxy citric acid, and compositions containing the potassium hydroxy cit ric acid
US7927636B1 (en) 1997-07-14 2011-04-19 Interhealth Nutraceuticals, Inc. Hydroxycitric acid compositions, pharmaceutical and dietary supplements and food products made therefrom, and methods for their use in reducing body weight
US6447807B1 (en) * 1999-09-14 2002-09-10 Dallas L. Clouatre Potassium (-)-hydroxycitric acid methods for pharmaceutical preparations for stable and controlled delivery
WO2003092730A1 (fr) 2002-04-30 2003-11-13 Unibar Corporation Composition de sel d'acide hydroxycitrique et procede de fabrication

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5536516A (en) * 1994-08-24 1996-07-16 Renaissance Herbs, Inc. Hydroxycitric acid concentrate and food products prepared therefrom
US5656314A (en) * 1994-08-24 1997-08-12 Moffett; Scott Alexander Hydroxycitric acid concentrate and food products prepared therefrom
US6221901B1 (en) * 1996-10-22 2001-04-24 Ravi Shrivastava Magnesium (-)hydroxycitrate, method of preparation, applications, and compositions in particular pharmaceutical containing same
EP0866137A1 (fr) * 1997-03-17 1998-09-23 Lupin Laboratories Limited Procédé de préparation de (-)-érythrohydroxycitrate de calcium
US6395296B1 (en) * 1997-08-08 2002-05-28 Karanam Balasubramanyam Soluble double metal salt of group IA and IIA of hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties
US6147228A (en) * 1998-08-03 2000-11-14 Department Of Science And Technology Government Of India Convenient method for the large scale isolation of garcinia acid
US6482858B1 (en) * 2001-06-20 2002-11-19 Dallas L Clouatre (−)-hydroxycitric acid for wound healing and immunomodulation

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007010838A1 (fr) * 2005-07-15 2007-01-25 Nippon Shinyaku Co., Ltd. Procédé servant à produire un sel de métal alcalinoterreux de l'acide (-)-hydroxycitrique
JP4998264B2 (ja) * 2005-07-15 2012-08-15 日本新薬株式会社 （−）−ヒドロキシクエン酸のアルカリ土類金属塩の製造法
WO2018049216A1 (fr) 2016-09-08 2018-03-15 Glykon Technologies Group, Llc Composés d'acide hydroxycitrique bimétalliques monomères et leurs procédés de fabrication et utilisation
CN110087646A (zh) * 2016-09-08 2019-08-02 格利康科技集团有限责任公司 单体双金属羟基柠檬酸化合物及其制备和使用方法
EP3509578A4 (fr) * 2016-09-08 2020-05-27 Glykon Technologies Group, LLC Composés d'acide hydroxycitrique bimétalliques monomères et leurs procédés de fabrication et utilisation
US11066423B2 (en) 2016-09-08 2021-07-20 Glykon Technologies Group, Llc Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same
US11292759B2 (en) * 2018-03-07 2022-04-05 Nutrition Research Group, Limited Hydroxycitric acid metal heterocyclic compounds with covalent characteristics

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Publication number Publication date
US7214823B2 (en) 2007-05-08
AU2003241151A1 (en) 2004-12-03
US20040259937A1 (en) 2004-12-23

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